HUT53598A - Process for production of derivatives of amin acid and medical compositions containing them as active substance - Google Patents

Process for production of derivatives of amin acid and medical compositions containing them as active substance Download PDF

Info

Publication number: HUT53598A
Authority: HU; Hungary
Prior art keywords: formula; butyl; group; isopropyl; tert
Prior art date: 1989-04-05

Application number

HU902037A

Other languages

English (en)

Hungarian (hu)

Other versions

HU902037D0 (en

Inventor

Quirico Branca

Hans Peter Marki

Werner Neidhart

Henri Ramuz

Wolfgang Wostl

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-04-05

Filing date

1990-04-02

Publication date

1990-11-28

1990-04-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1990-08-28 Publication of HU902037D0 publication Critical patent/HU902037D0/hu

1990-11-28 Publication of HUT53598A publication Critical patent/HUT53598A/hu

Links

238000000034 method Methods 0.000 title claims description 55
239000000203 mixture Substances 0.000 title claims description 50
239000002253 acid Substances 0.000 title claims description 40
230000008569 process Effects 0.000 title claims description 27
238000004519 manufacturing process Methods 0.000 title description 4
239000013543 active substance Substances 0.000 title 1
-1 benzyloxylcarbonyl Chemical group 0.000 claims description 145
150000001875 compounds Chemical class 0.000 claims description 88
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 43
239000007858 starting material Substances 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 21
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
125000001589 carboacyl group Chemical group 0.000 claims description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
206010020772 Hypertension Diseases 0.000 claims description 7
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000003884 phenylalkyl group Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
150000001413 amino acids Chemical class 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 6
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 6
108010016626 Dipeptides Proteins 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
241001024304 Mino Species 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims description 2
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 2
WAMWSIDTKSNDCU-ZETCQYMHSA-N (2s)-2-azaniumyl-2-cyclohexylacetate Chemical compound OC(=O)[C@@H](N)C1CCCCC1 WAMWSIDTKSNDCU-ZETCQYMHSA-N 0.000 claims 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 1
208000023514 Barrett esophagus Diseases 0.000 claims 1
206010012735 Diarrhoea Diseases 0.000 claims 1
GEYBMYRBIABFTA-VIFPVBQESA-N O-methyl-L-tyrosine Chemical compound COC1=CC=C(C[C@H](N)C(O)=O)C=C1 GEYBMYRBIABFTA-VIFPVBQESA-N 0.000 claims 1
GNADVDLLGVSXLS-ULQDDVLXSA-N Pro-Phe-His Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O GNADVDLLGVSXLS-ULQDDVLXSA-N 0.000 claims 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
150000003862 amino acid derivatives Chemical class 0.000 claims 1
125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 claims 1
UCVVDURPZNVMNR-VIFPVBQESA-N naphthalen-1-yl (2s)-2-aminopropanoate Chemical compound C1=CC=C2C(OC(=O)[C@@H](N)C)=CC=CC2=C1 UCVVDURPZNVMNR-VIFPVBQESA-N 0.000 claims 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
150000005331 phenylglycines Chemical class 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 216
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 82
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
239000011541 reaction mixture Substances 0.000 description 55
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 36
229910002027 silica gel Inorganic materials 0.000 description 36
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
239000003921 oil Substances 0.000 description 26
235000019198 oils Nutrition 0.000 description 26
125000006239 protecting group Chemical group 0.000 description 26
239000000284 extract Substances 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
229940080818 propionamide Drugs 0.000 description 14
238000003756 stirring Methods 0.000 description 14
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 13
150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
206010057190 Respiratory tract infections Diseases 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 11
125000000753 cycloalkyl group Chemical group 0.000 description 11
239000000047 product Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000006260 foam Substances 0.000 description 10
239000005457 ice water Substances 0.000 description 10
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
125000000160 oxazolidinyl group Chemical group 0.000 description 9
238000000746 purification Methods 0.000 description 9
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229940024606 amino acid Drugs 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
235000001014 amino acid Nutrition 0.000 description 7
229960002885 histidine Drugs 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000011347 resin Substances 0.000 description 7
229920005989 resin Polymers 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
125000000168 pyrrolyl group Chemical group 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000000126 substance Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
210000004556 brain Anatomy 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000010828 elution Methods 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
229960005190 phenylalanine Drugs 0.000 description 5
230000007017 scission Effects 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 4
125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
235000014676 Phragmites communis Nutrition 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
108090000783 Renin Proteins 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000000872 buffer Substances 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000002024 ethyl acetate extract Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
206010020843 Hyperthermia Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
230000036186 satiety Effects 0.000 description 1
235000019627 satiety Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
VIGBIBDAVDHOTP-UHFFFAOYSA-M sodium;ethanol;acetate Chemical compound [Na+].CCO.CC([O-])=O VIGBIBDAVDHOTP-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229940033123 tannic acid Drugs 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229910000648 terne Inorganic materials 0.000 description 1
QKSQWQOAUQFORH-VAWYXSNFSA-N tert-butyl (ne)-n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)\N=N\C(=O)OC(C)(C)C QKSQWQOAUQFORH-VAWYXSNFSA-N 0.000 description 1
BOGFJNTUIVHTMN-UHFFFAOYSA-N tert-butyl 1,3-oxazolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1NCCO1 BOGFJNTUIVHTMN-UHFFFAOYSA-N 0.000 description 1
AMZJHBQITVMFNI-UHFFFAOYSA-N tert-butyl 1,3-oxazolidine-3-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOC1 AMZJHBQITVMFNI-UHFFFAOYSA-N 0.000 description 1
SUEKOLPTYLFNIN-UHFFFAOYSA-N tert-butyl 2-methyl-1,3-oxazolidine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1C(OCC1)C SUEKOLPTYLFNIN-UHFFFAOYSA-N 0.000 description 1
UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
PIGOINQOOIRRHS-UHFFFAOYSA-N tert-butyl 4-(cyclohexylmethyl)-5-[2-(2-hydroxyethyl)-3-methylbutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate Chemical compound OCCC(C(C)C)CC1OC(C)(C)N(C(=O)OC(C)(C)C)C1CC1CCCCC1 PIGOINQOOIRRHS-UHFFFAOYSA-N 0.000 description 1
XEQFLJBHYPRWFF-UHFFFAOYSA-N tert-butyl 5-(3-amino-3-oxopropyl)-1h-imidazole-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=NC=C(CCC(N)=O)N1 XEQFLJBHYPRWFF-UHFFFAOYSA-N 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
239000005460 tetrahydrofolate Substances 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
238000004448 titration Methods 0.000 description 1
RLUJQBLWUQZMDG-UHFFFAOYSA-N toluene;hydrochloride Chemical compound Cl.CC1=CC=CC=C1 RLUJQBLWUQZMDG-UHFFFAOYSA-N 0.000 description 1
230000026683 transduction Effects 0.000 description 1
238000010361 transduction Methods 0.000 description 1
HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229960004441 tyrosine Drugs 0.000 description 1
239000004474 valine Substances 0.000 description 1
239000007966 viscous suspension Substances 0.000 description 1
239000011800 void material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0823—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Animal Behavior & Ethology (AREA)
Crystallography & Structural Chemistry (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Thiazole And Isothizaole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HU902037A 1989-04-05 1990-04-02 Process for production of derivatives of amin acid and medical compositions containing them as active substance HUT53598A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH129089		1989-04-05

Publications (2)

Publication Number	Publication Date
HU902037D0 HU902037D0 (en)	1990-08-28
HUT53598A true HUT53598A (en)	1990-11-28

Family

ID=4206973

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU902037A HUT53598A (en)	1989-04-05	1990-04-02	Process for production of derivatives of amin acid and medical compositions containing them as active substance

Country Status (15)

Country	Link
US (1)	US5140011A (de)
EP (1)	EP0391179A3 (de)
JP (1)	JPH02290836A (de)
KR (1)	KR900016114A (de)
AU (1)	AU5252290A (de)
CA (1)	CA2012901A1 (de)
FI (1)	FI901730A7 (de)
HU (1)	HUT53598A (de)
IL (1)	IL93955A0 (de)
MC (1)	MC2107A1 (de)
NO (1)	NO901533L (de)
NZ (1)	NZ233082A (de)
PT (1)	PT93658A (de)
YU (1)	YU65690A (de)
ZA (1)	ZA902444B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2209937B (en) *	1987-09-21	1991-07-03	Depiopharm S A	Water insoluble polypeptides
US5250517A (en) *	1987-10-06	1993-10-05	Hoffmann-La Roche Inc.	Renin inhibiting compounds
CA1328333C (en) *	1988-03-04	1994-04-05	Quirico Branca	Amino acid derivatives
US5430041A (en) *	1991-05-10	1995-07-04	Hoffmann-La Roche Inc.	Amino acid derivatives having antiviral activity
US7141609B2 (en)	1992-08-25	2006-11-28	G.D. Searle & Co.	α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
ES2123065T3 (es)	1992-08-25	1999-01-01	Searle & Co	Hidroxietilamino-sulfonamidas utiles como inhibidores de proteasas retroviricas.
US5326773A (en) *	1992-10-29	1994-07-05	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
EP0741696A1 (de) *	1994-01-25	1996-11-13	G.D. SEARLE & CO.	Malaria aspartic protease hemmende verbindungen
US5777153A (en) *	1994-07-08	1998-07-07	Gilead Sciences, Inc.	Cationic lipids
US6093816A (en) *	1996-06-27	2000-07-25	Isis Pharmaceuticals, Inc.	Cationic lipids
EP1095022A1 (de)	1998-07-08	2001-05-02	G.D. Searle & Co.	Inhibitoren von retoviraler protease
JP2008266292A (ja) *	2007-03-23	2008-11-06	Sumitomo Chemical Co Ltd	ベンゾアゾール化合物の製造方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8322414D0 (en) *	1983-08-19	1983-09-21	Szelke M	Renin inhibitors
US4613676A (en) *	1983-11-23	1986-09-23	Ciba-Geigy Corporation	Substituted 5-amino-4-hydroxyvaleryl derivatives
US4652551A (en) *	1984-06-22	1987-03-24	Abbott Laboratories	Renin inhibiting compounds
US4880781A (en) *	1984-08-06	1989-11-14	The Upjohn Company	Renin inhibitory peptides containing an N-alkyl-histidine moiety
US4727060A (en) *	1984-11-13	1988-02-23	Ciba-Geigy Corporation	Novel 5-amino-4-hydroxyvaleryl derivatives
IL81234A (en) *	1986-01-16	1992-09-06	Abbott Lab	Peptidylaminodiols,process for their preparation and pharmaceutical compositions comprising them
EP0264106B1 (de) *	1986-10-14	1994-03-16	Banyu Pharmaceutical Co., Ltd.	5-Substituierte Amino-4-hydroxy-pentansäure-Derivate und deren Verwendung
US4758584A (en) *	1987-02-05	1988-07-19	Ciba-Geigy Corporation	Antihypertensive 5-amino-4-hydroxyvaleryl derivatives substituted by sulphur-containing groups
DK523288A (da) *	1987-10-06	1989-04-07	Hoffmann La Roche	Aminosyrederivater

1990
- 1990-03-23 CA CA002012901A patent/CA2012901A1/en not_active Abandoned
- 1990-03-24 EP EP19900105613 patent/EP0391179A3/de not_active Withdrawn
- 1990-03-26 NZ NZ233082A patent/NZ233082A/xx unknown
- 1990-03-29 US US07/501,694 patent/US5140011A/en not_active Expired - Fee Related
- 1990-03-29 MC MC902123A patent/MC2107A1/fr unknown
- 1990-03-29 ZA ZA902444A patent/ZA902444B/xx unknown
- 1990-03-30 IL IL9093955A patent/IL93955A0/xx unknown
- 1990-04-02 AU AU52522/90A patent/AU5252290A/en not_active Abandoned
- 1990-04-02 HU HU902037A patent/HUT53598A/hu unknown
- 1990-04-03 KR KR1019900004555A patent/KR900016114A/ko not_active Withdrawn
- 1990-04-04 JP JP2090058A patent/JPH02290836A/ja active Pending
- 1990-04-04 YU YU00656/90A patent/YU65690A/xx unknown
- 1990-04-04 PT PT93658A patent/PT93658A/pt not_active Application Discontinuation
- 1990-04-04 NO NO90901533A patent/NO901533L/no unknown
- 1990-04-05 FI FI901730A patent/FI901730A7/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO901533D0 (no)	1990-04-04
MC2107A1 (fr)	1991-03-11
CA2012901A1 (en)	1990-10-05
EP0391179A3 (de)	1991-04-03
ZA902444B (en)	1990-12-28
US5140011A (en)	1992-08-18
PT93658A (pt)	1990-11-20
KR900016114A (ko)	1990-11-12
EP0391179A2 (de)	1990-10-10
JPH02290836A (ja)	1990-11-30
FI901730A7 (fi)	1990-10-06
NO901533L (no)	1990-10-08
YU65690A (en)	1991-10-31
HU902037D0 (en)	1990-08-28
NZ233082A (en)	1992-11-25
FI901730A0 (fi)	1990-04-05
IL93955A0 (en)	1990-12-23
AU5252290A (en)	1990-11-22

Legal Events

Date	Code	Title	Description
1993-06-28	DFC9	Refusal of application

Publication	Publication Date	Title
TW412512B (en)	2000-11-21	Non-peptide tachykinin receptor antagonists
DE69129248T2 (de)	1998-08-06	Peptide mit Endothelin antagonistischer Aktivität, deren Herstellung und pharmazeutische Zusammensetzungen
AU2008244305B2 (en)	2013-08-01	Novel tetrahydrocarbazole derivatives as ligands of G-protein coupled receptors
US11291731B2 (en)	2022-04-05	Silicon based drug conjugates and methods of using same
TW509698B (en)	2002-11-11	Inhibitors of interleukin-1β converting enzyme
AU735075B2 (en)	2001-06-28	Inhibitors of interleukin-1beta converting enzyme
DK1427423T5 (da)	2018-04-09	Benzothiazepin] og benzothiadiazepinderivater med ileal galdesyretransport] (IBAT) inhiberende aktivitet til behandling af hyperlipidami
HUT53598A (en)	1990-11-28	Process for production of derivatives of amin acid and medical compositions containing them as active substance
WO1996033212A1 (fr)	1996-10-24	Nouveaux derives peptidiques
UA76977C2 (en)	2006-10-16	Aryl- and heteroaryl substituted chk1 inhibitors and their use as radiosensitizers and chemosensitizers
HU230123B1 (hu)	2015-08-28	Szubsztituált indolil-oxo-acetil-piperazinszármazékok, ezeket tartalmazó készítmények és vírusellenes alkalmazásuk
HU229404B1 (en)	2013-12-30	1,2-annelated quinoline derivatives
EP2976341B1 (de)	2018-02-28	Acyclische cyanoethylpyrazolpyridone als januskinaseinhibitoren
HUT72076A (en)	1996-03-28	Process for preparing spiro piperidines and homologs which promote release of growth hormone and pharmaceutical compositions containing them
JPH06116245A (ja)	1994-04-26	２，４−ジオキソ−イミダゾリジン−誘導体
JP2019537603A (ja)	2019-12-26	アルファｖインテグリン阻害剤としてのアゾールアミドおよびアミン
US4985407A (en)	1991-01-15	Dipeptide compounds, processes for their preparation and compositions containing them
UA127808C2 (uk)	2024-01-10	Похідна пладієноліду (варіанти) як засіб, що здійснює цілеспрямований вплив на сплайсосому, для лікування раку
AU2017229591B2 (en)	2021-08-19	Calpain modulators and methods of production and use thereof
JPH02300199A (ja)	1990-12-12	レトロウイルスプロテアーゼ阻害剤
AU605212B2 (en)	1991-01-10	Renin-inhibitors III
US4826814A (en)	1989-05-02	Tripeptide derivatives
TW200410986A (en)	2004-07-01	Pharamaceutical comiposition comprising cyclic somatostatin analogs II
JPH06508137A (ja)	1994-09-14	レニン抑制剤としてのヒドロキシアジド誘導体および関連化合物
EP4659764A1 (de)	2025-12-10	Linker-wirkstoff und herstellungsverfahren und verwendung eines antikörper-wirkstoff-konjugats davon